Diethyl aminosulfur trifluoride → 2-Dodecyl-alpha-fluoro-alpha-phenyl-2H-tetrazole-5-acetic acid, ethyl ester

HRID 1756918Notes

Reaction equation

HRID 1756918 reaction equation
[CH2:1]([N:13]1[N:17]=[N:16][C:15]([C:18](O)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N:14]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C(S(F)(F)([F:37])(CC)N)C>C(Cl)Cl>[CH2:1]([N:13]1[N:17]=[N:16][C:15]([C:18]([F:37])([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N:14]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 53748433Diethyl aminosulfur trifluorideHCID 867482832-dodecyl-alpha-hydroxy-alpha-phenyl-2H-tetrazole-5-acetic acid, ethyl ester

Product 1

HCID 586632482-Dodecyl-alpha-fluoro-alpha-phenyl-2H-tetrazole-5-acetic acid, ethyl esterYield 66.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of 2-dodecyl-α-hydroxy-α-phenyl-2H-tetrazole-5-acetic acid, ethyl ester (0.45 g, 1.08 mmole) in CH2Cl2 (2 mL) was added dropwise to a -78° C. solution of diethyl amino sulfur trifluoride (DAST, J. Org. Chem. 1975;(40):574:578, 0.15 mL, 1.1 mmole) in CH2Cl2 (1 mL) under dry nitrogen. The mixture was stirred for 60 minutes at -78° C. before the cooling bath was removed and the solution allowed to warm to room temperature, where it was stirred an additional 3 hours. The mixture was poured into ice water and extracted with ethyl acetate (2×100 mL). The combined ethyl acetate extracts were washed with brine (50 mL) and dried. Filtration and concentration produced an oil which was flash chromatographed (silica gel, 7:1 hexane-ethyl acetate) to afford 0.3 g (66%) of the title compound as an oil.

Workup

  1. customwas removed
  2. temperatureto warm to room temperature
  3. stirringwhere it was stirred an additional 3 hours
  4. additionThe mixture was poured into ice water
  5. extractionextracted with ethyl acetate (2×100 mL)
  6. washThe combined ethyl acetate extracts were washed with brine (50 mL)
  7. customdried
  8. filtrationFiltration and concentration
  9. customproduced an oil which
  10. customchromatographed (silica gel, 7:1 hexane-ethyl acetate)

Sources & evidence

ORD record
ord-d455c4620db04ddf82e977e099887a54
Source dataset
uspto-grants-1995_08
Patent number
US05441975

Reaction notes

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